Synthetic process of double-long-chain diester quaternary ammonium salt

A diester-based quaternary ammonium salt and a synthesis process technology, which is applied in the preparation of amino hydroxyl compounds, the preparation of organic compounds, organic chemistry, etc., can solve the problems of carcinogenicity, high toxicity, and low content of double long-chain esteramines, and achieve no The effects of three wastes generation, mild reaction conditions, and easy separation and purification

Inactive Publication Date: 2012-05-02
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many deficiencies in the above synthesis process, for example: the content of double long-chain ester amines in the obtained ester amine mixture is low; the toxicity of alkylating reagents such as dimethyl sulfate and methyl halide is very high or there is the possibility of carcinogenicity, etc.

Method used

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  • Synthetic process of double-long-chain diester quaternary ammonium salt
  • Synthetic process of double-long-chain diester quaternary ammonium salt
  • Synthetic process of double-long-chain diester quaternary ammonium salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Weigh 11.92g (0.1mol) of N-methyldiethanolamine and 14.17g (0.13mol) of bromoethane into a 250mL three-necked flask, add 30mL of methanol as a solvent, and heat it in a water bath to 35°C for constant temperature reaction Stop at 4h, remove methanol by rotary evaporation, use ethyl acetate-methanol mixed solvent to recrystallize to obtain white crystal substance N-methylethyldihydroxyethylammonium bromide; weigh N-methylethyldihydroxyethylammonium bromide Ammonium 11.41g (0.05mol) was added to a 250mL three-necked flask, an appropriate amount of solvent chloroform and acid agent triethylamine were added, and 30.30g (0.10mol) of stearyl chloride was slowly added dropwise in an ice-water bath, and the temperature rose naturally after the addition Reaction at room temperature for 8h, stop the reaction. The solvent was removed by rotary evaporation, and the white solid product N-methyl ethyl distearate ethyl ammonium bromide was obtained by recrystallization thre...

Embodiment 2

[0022] Example 2: Weigh 11.92g (0.1mol) of N-methyldiethanolamine and 14.17g (0.13mol) of bromoethane, add them to a 250mL three-necked flask, add 35mL of ethanol as a solvent, and heat in a water bath to 45°C for constant temperature reaction Stop at 5h, remove ethanol by rotary evaporation, use ethyl acetate-methanol mixed solvent to recrystallize to obtain white crystal substance N-methylethyldihydroxyethylammonium bromide; weigh N-methylethyldihydroxyethylammonium bromide Ammonium 11.41g (0.05mol) was added to a 250mL three-necked flask, an appropriate amount of solvent chloroform and acid agent triethylamine were added, and 33.33g (0.11mol) of stearyl chloride was slowly added dropwise in an ice-water bath, and the temperature rose naturally after the addition To room temperature reaction 10h, stop the reaction. The solvent was removed by rotary evaporation, and the white solid product N-methyl ethyl distearate ethyl ammonium bromide was obtained by recrystallization thre...

Embodiment 3

[0023] Example 3: Weigh 11.92g (0.1mol) of N-methyldiethanolamine and 15.26g (0.14mol) of bromoethane into a 250mL three-necked flask, add 40mL of acetone as a solvent, and heat it in a water bath to 50°C for constant temperature reaction Stop at 4h, remove acetone by rotary evaporation, and use ethyl acetate-methanol mixed solvent to recrystallize to obtain white crystal substance N-methylethyl dihydroxyethyl ammonium bromide; weigh N-methyl ethyl dihydroxyethyl ammonium bromide Ammonium 11.41g (0.05mol) was added to a 250mL three-necked flask, an appropriate amount of solvent chloroform and acid agent triethylamine were added, and 30.30g (0.10mol) of stearyl chloride was slowly added dropwise in an ice-water bath, and the temperature rose naturally after the addition To room temperature reaction 10h, stop the reaction. The solvent was removed by rotary evaporation, and the white solid product N-methyl ethyl distearate ethyl ammonium bromide was obtained by recrystallization ...

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Abstract

The invention provides a double-long-chain diester quaternary ammonium salt. Diester is introduced into a molecular structure, so that the degradability is enhanced greatly, and environmental friendliness is realized. The invention further provides a synthetic process of the double-long-chain diester quaternary ammonium salt. The process comprises the following steps of: mixing N-methyl diethanolamine with short-chain alkyl halide, adding an appropriate amount of solvent, and reacting under certain reaction conditions to obtain dihydroxyethyl ammonium halide serving as a reaction intermediate; mixing the dihydroxyethyl ammonium halide with long-chain alkyl acyl chloride, adding an appropriate amount of solvent, and reacting under certain reaction conditions; and performing rotary steaming at the end of the reaction and repeatedly recrystallizing to obtain a final solid product. In the synthetic process, a nonconventional quaternary ammonium salt synthesis route for quaternary amination and esterifying in sequence is adopted, so that the raw material transformation ratio is high, an intermediate product is easy to separate and purify, the reaction conditions are mild, the final product is in light color and has high active matter content, the solvent can be recycled, no three wastes is produced, and the use of the conventional toxic alkylation reagents such as dimethyl sulfate, halomethane and the like is avoided in the synthetic process.

Description

technical field [0001] The invention relates to a synthesis process of a double long-chain diester group quaternary ammonium salt, belonging to the technical field of surfactants. Background technique [0002] Quaternary ammonium salt cationic surfactant is a kind of surfactant with high output and wide application. It has strong detergency and bactericidal effect. It can be used as waterproof softener, wetting agent, anti-shrinkage agent, antistatic agent for fiber treatment In addition, it is also widely used in pharmaceuticals, papermaking, metal surface treatment, flotation, chemical fiber oil agents, cosmetics and oil field development. [0003] With the development of the surfactant industry and the enhancement of people's awareness of environmental protection, exploring new surfactants with excellent synthetic performance and environmental friendliness has become a research hotspot. Ester quaternary ammonium salt is a new type of cationic surfactant with excellent so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C219/06C07C213/06B01F17/18C09K23/18
Inventor 范明明魏小桥倪邦庆
Owner JIANGNAN UNIV
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